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Remote electron effects and π-π interactions of α-diimine nickel complexes

  • Hefei National Research Center for Physical Sciences at the Microscale, CAS Key Laboratory of Soft Matter Chemistry, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei 230026, China

Cite this:
CSTR: 32290.14.JUSTC-2024-0059
https://doi.org/10.52396/JUSTC-2024-0059
More Information
  • Author Bio:

    Yizhan Wang is currently a master’s student in the Department of Polymer Science and Engineering, University of Science and Technology of China, under the supervision of Prof. Changle Chen. His research mainly focuses on the preparation of α-diimine nickel catalysts and their applications in olefin polymerization

    Hailong He is currently a graduate student in the Department of Polymer Science and Engineering, University of Science and Technology of China, under the supervision of Prof. Changle Chen. His research mainly focuses on the preparation of nickel and palladium catalysts and their applications in olefin polymerization

    Dan Peng is currently a postdoctoral researcher in the Hefei National Research Center for Physical Sciences at the Microscale, University of Science and Technology of China (USTC). She received her Ph.D. degree from USTC under the tutelage of Prof. Changle Chen in 2023. Her research interests include the preparation of polyolefin materials and their applications

  • Corresponding author: E-mail: pengdan@ustc.edu.cn
  • Received Date: 24 April 2024
  • Accepted Date: 19 June 2024
    Abstract

  • Abstract

    The seminal report of α-diimine palladium and nickel catalysts in 1995 represented a major breakthrough in the preparation of functionalized polyolefin materials. Owing to the high abundance and low cost of nickel, nickel-based catalysts have great application prospects in the industrialization process of olefin coordination polymerization. In this work, various N-aryl substituents with different electronic effects were synthesized and introduced into α-diimine ligands. The as-prepared α-diimine nickel catalysts showed high polymerization activity (0.9×107–3.0×107 g·mol−1·h−1) in ethylene polymerization, generating polyethylene products with adjustable molecular weights (Mn values: 7.4×104–146.9×104 g·mol−1) and branching densities (31/1000 C–68/1000 C). The resulting polyethylene products showed excellent mechanical properties, with high tensile strength (up to 25.0 MPa) and high strain at break values (up to 3890%). The copolymerization of ethylene and polar monomers can also be achieved by these nicekel complexes, ultimately preparing functionalized polyolefins.

    Graphical abstract

    New types of α-diimine nickel catalysts with remote electron effects and π-π interactions were prepared and used in ethylene (co) polymerization.

    Abstract

    The seminal report of α-diimine palladium and nickel catalysts in 1995 represented a major breakthrough in the preparation of functionalized polyolefin materials. Owing to the high abundance and low cost of nickel, nickel-based catalysts have great application prospects in the industrialization process of olefin coordination polymerization. In this work, various N-aryl substituents with different electronic effects were synthesized and introduced into α-diimine ligands. The as-prepared α-diimine nickel catalysts showed high polymerization activity (0.9×107–3.0×107 g·mol−1·h−1) in ethylene polymerization, generating polyethylene products with adjustable molecular weights (Mn values: 7.4×104–146.9×104 g·mol−1) and branching densities (31/1000 C–68/1000 C). The resulting polyethylene products showed excellent mechanical properties, with high tensile strength (up to 25.0 MPa) and high strain at break values (up to 3890%). The copolymerization of ethylene and polar monomers can also be achieved by these nicekel complexes, ultimately preparing functionalized polyolefins.

    • Public Summary

    • Novel α-diimine nickel catalysts with different electronic effects were prepared.
    • These α-diimine nickel catalysts showed high polymerization activities in ethylene polymerization, generating polyethylene products with adjustable molecular weight and branching density.
    • These α-diimine nickel catalysts can also catalyze the copolymerization of ethylene and polar monomer, preparing functionalized polyolefin.

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    • References(47)
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    Wu R K, Wu W K, Stieglitz L, et al. Recent advances on α-diimine Ni and Pd complexes for catalyzed ethylene (Co)polymerization: A comprehensive review. Coordination Chemistry Reviews, 2023, 474: 214844. doi: 10.1016/j.ccr.2022.214844
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    Zhang D F, Nadres E T, Brookhart M, et al. Synthesis of highly branched polyethylene using “sandwich” (8- p-tolyl naphthyl α-diimine)nickel(II) catalysts. Organometallics, 2013, 32: 5136–5143. doi: 10.1021/om400704h
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    Lian K B, Zhu Y, Li W M, et al. Direct synthesis of thermoplastic polyolefin elastomers from nickel-catalyzed ethylene polymerization. Macromolecules, 2017, 50: 6074–6080. doi: 10.1021/acs.macromol.7b01087
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    Hu X Q, Wang C Q, Jian Z B. Comprehensive studies of the ligand electronic effect on unsymmetrical α-diimine nickel(II) promoted ethylene (co)polymerizations. Polymer Chemistry, 2020, 11: 4005–4012. doi: 10.1039/D0PY00536C
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    Wang Y Y, Wang C Q, Hu X Q. et al. Benzosuberyl substituents as a “sandwich-like” function in olefin polymerization catalysis. Chinese Journal of Polymer Science, 2021, 39: 984–993. doi: 10.1007/s10118-021-2562-7
    [30]
    Peng D, Xu M H, Tan C, et al. Emulsion polymerization strategy for heterogenization of olefin polymerization catalysts. Macromolecules, 2023, 56: 2388–2396. doi: 10.1021/acs.macromol.3c00261
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    Zhong L, Li G L, Liang G D, et al. Enhancing thermal stability and living fashion in α-diimine–nickel-catalyzed (co)polymerization of ethylene and polar monomer by increasing the steric bulk of ligand backbone. Macromolecules, 2017, 50: 2675–2682. doi: 10.1021/acs.macromol.7b00121
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    Figure  1.  Selected α-diimine nickel complexes.

    Figure  2.  Synthesis of α-diimine ligands L1–L3 and nickel catalysts Ni1–Ni3.

    Figure  3.  (a) Molecular structures of Ni2 (CCDC number 2348877).The selected bond lengths (Å) and angles (°) were as follows: Ni1–N1 2.025(2), Ni1–N2 2.025(2), Ni1–Br1 2.3315(4), Ni1–Br2 2.3315(4), N1–Ni1–N2 82.40(14), Br2–Ni1–Br1 115.38(3). (b) Molecular structures of Ni3 (CCDC number 2348878).The selected bond lengths (Å) and angles (°) were as follows: Ni1–N12.034(2), Ni1–N2 2.209(2), Ni1–Br1 2.4368(5), Ni1–Br2 2.3539(5), N1–Ni1–N2 80.15(9), Br2–Ni1–Br1 130.943(18).

    Figure  4.  (a) Stress‒strain curves of the polymer samples obtained from Ni1 at 50 °C, 80 °C and 100 °C. (b) Stress‒strain curves of the polymer samples obtained from Ni1–Ni3 at 80 °C. (c) Fracture stress and Young’s modulus of the polymer samples generated from Ni1–Ni3 at 80 °C. (d) Strain recovery curve of the polymer sample from Table 1, entry 3.

    [1]
    Tan C, Chen M, Zou C, et al. Potentially practical catalytic systems for olefin-polar monomer coordination copolymerization. CCS Chemistry, 2024, 6: 882–897. doi: 10.31635/ccschem.023.202303322
    [2]
    Franssen N M G, Reek J N H, de Bruin B. Synthesis of functional ‘polyolefins’: state of the art and remaining challenges. Chemical Society Reviews, 2013, 42: 5809–5832. doi: 10.1039/c3cs60032g
    [3]
    Chung T C. Functionalization of Polyolefins. New York: Academic Press, 2002 .
    [4]
    Tan C, Chen C L. Nickel catalysts for the synthesis of ultra-high molecular weight polyethylene. Science Bulletin, 2020, 65: 1137–1138. doi: 10.1016/j.scib.2020.04.009
    [5]
    Soshnikov I E, Chen C L, Bryliakov K P. Ni catalyzed ethylene copolymerization with polar monomers. Science China Chemistry, 2019, 62: 653–654. doi: 10.1007/s11426-019-9458-7
    [6]
    Xiong S, Shoshani M M, Zhang X, et al. Effcient copolymerization of acrylate and ethylene with neutral P, O-chelated nickel catalysts: mechanistic investigations of monomer insertion and chelate formation. Journal of the American Chemical Society, 2021, 143: 6516–6527. doi: 10.1021/jacs.1c00566
    [7]
    Hu X Q, Kang X H, Jian Z B. Suppression of chain transfer at high temperature in catalytic olefin polymerization. Angewandte Chemie International Edition, 2022, 61: e202207363. doi: 10.1002/anie.202207363
    [8]
    Li M Y, Cai Z G, Eisen M S. Rational design of aldimine imidazolidin-2-imine/guanidine nickel catalysts for norbornene (co)polymerizations with enhanced catalytic performance. Journal of Catalysis, 2023, 420: 58–67. doi: 10.1016/j.jcat.2023.02.015
    [9]
    Tan C, Chen C L. Emerging palladium and nickel catalysts for copolymerization of olefins with polar monomers. Angewandte Chemie International Edition, 2019, 58: 7192–7200. doi: 10.1002/anie.201814634
    [10]
    Tan C, Zou C, Chen C L. Material properties of functional polyethylenes from transition-metal-catalyzed ethylene–polar monomer copolymerization. Macromolecules, 2022, 55: 1910–1922. doi: 10.1021/acs.macromol.2c00058
    [11]
    Boaen N K, Hillmyer M A. Post-polymerization functionalization of polyolefins. Chemical Society Reviews, 2005, 34: 267–275. doi: 10.1039/b311405h
    [12]
    Muhammad Q, Tan C, Chen C L. Concerted steric and electronic effects on α-diimine nickel- and palladium-catalyzed ethylene polymerization and copolymerization. Science Bulletin, 2020, 65: 300–307. doi: 10.1016/j.scib.2019.11.019
    [13]
    Yuan W B, Li W M, Dai S Y. Preparation of polyethylene thermoplastic elastomers using CS-symmetric nickel catalysts in ethylene polymerization. Polymer, 2023, 285: 126322. doi: 10.1016/j.polymer.2023.126322
    [14]
    Yan Z P, Chang G R, Zou W P, et al. Synthesis of lightly branched ultrahigh-molecular-weight polyethylene using cationic benzocyclohexyl nickel catalysts. Polymer Chemistry, 2023, 14: 183–190. doi: 10.1039/D2PY01087A
    [15]
    Johnson L K, Killian C M, Brookhart M. New Pd(II)- and Ni(II)-based catalysts for polymerization of ethylene and α-olefins. Journal of the American Chemical Society, 1995, 117: 6414–6415. doi: 10.1021/ja00128a054
    [16]
    Wang F Z, Chen C L. A continuing legend: the brookhart-type α-diimine nickel and palladium catalysts. Polymer Chemistry, 2019, 10: 2354–2369. doi: 10.1039/C9PY00226J
    [17]
    Guo L H, Dai S Y, Sui X L, et al. Palladium and nickel catalyzed chain walking olefin polymerization and copolymerization. ACS Catalysis, 2016, 6: 428–441. doi: 10.1021/acscatal.5b02426
    [18]
    Popeney C S, Levins C M, Guan Z. Systematic investigation of ligand substitution effects in cyclophane-based nickel(II) and palladium(II) olefin polymerization catalysts. Organometallics, 2011, 30: 2432–2452. doi: 10.1021/om200193r
    [19]
    Rhinehart J L, Mitchell N E, Long B K. Enhancing α-diimine catalysts for high-temperature ethylene polymerization. ACS Catalysis, 2014, 4: 2501–2504. doi: 10.1021/cs500694m
    [20]
    Wu R K, Wu W K, Stieglitz L, et al. Recent advances on α-diimine Ni and Pd complexes for catalyzed ethylene (Co)polymerization: A comprehensive review. Coordination Chemistry Reviews, 2023, 474: 214844. doi: 10.1016/j.ccr.2022.214844
    [21]
    Dai J J, Dai S Y. Impact of o-aryl halogen effects on ethylene polymerization: steric vs. electronic effects. Dalton Transactions, 2024, 53: 9286–9293. doi: 10.1039/D4DT00850B
    [22]
    Lu W Q, Ding B H, Zou W P, et al. Direct synthesis of polyethylene thermoplastic elastomers with high molecular weight and excellent elastic recovery via a hybrid steric bulky strategy. European Polymer Journal, 2023, 201: 112577. doi: 10.1016/j.eurpolymj.2023.112577
    [23]
    Ding B H, Jiang L H, Kang X H, et al. Enhancing suppression of chain transfer via catalyst structural evolution in ethylene (co)polymerization. Chinese Journal of Chemistry, 2023, 41: 1509–1516. doi: 10.1002/cjoc.202200842
    [24]
    Na Y N, Wang X B, Lian K B, et al. Dinuclear α-diimine NiII and PdII complexes that catalyze ethylene polymerization and copolymerization. ChemCatChem, 2017, 9: 1062–1066. doi: 10.1002/cctc.201601500
    [25]
    Zhang D F, Nadres E T, Brookhart M, et al. Synthesis of highly branched polyethylene using “sandwich” (8- p-tolyl naphthyl α-diimine)nickel(II) catalysts. Organometallics, 2013, 32: 5136–5143. doi: 10.1021/om400704h
    [26]
    Rhinehart J L, Brown L A, Long B K. A robust Ni(II) α-diimine catalyst for high temperature ethylene polymerization. Journal of the American Chemical Society, 2013, 135: 16316–16319. doi: 10.1021/ja408905t
    [27]
    Lian K B, Zhu Y, Li W M, et al. Direct synthesis of thermoplastic polyolefin elastomers from nickel-catalyzed ethylene polymerization. Macromolecules, 2017, 50: 6074–6080. doi: 10.1021/acs.macromol.7b01087
    [28]
    Hu X Q, Wang C Q, Jian Z B. Comprehensive studies of the ligand electronic effect on unsymmetrical α-diimine nickel(II) promoted ethylene (co)polymerizations. Polymer Chemistry, 2020, 11: 4005–4012. doi: 10.1039/D0PY00536C
    [29]
    Wang Y Y, Wang C Q, Hu X Q. et al. Benzosuberyl substituents as a “sandwich-like” function in olefin polymerization catalysis. Chinese Journal of Polymer Science, 2021, 39: 984–993. doi: 10.1007/s10118-021-2562-7
    [30]
    Peng D, Xu M H, Tan C, et al. Emulsion polymerization strategy for heterogenization of olefin polymerization catalysts. Macromolecules, 2023, 56: 2388–2396. doi: 10.1021/acs.macromol.3c00261
    [31]
    Zhong L, Li G L, Liang G D, et al. Enhancing thermal stability and living fashion in α-diimine–nickel-catalyzed (co)polymerization of ethylene and polar monomer by increasing the steric bulk of ligand backbone. Macromolecules, 2017, 50: 2675–2682. doi: 10.1021/acs.macromol.7b00121
    [32]
    Nie N, Yu F, Liu B Y, et al. Homo- and hetero-polymerization of ethylene catalyzed by α-diimine nickel complexes with hydroxyl groups. European Polymer Journal, 2024, 210: 112962. doi: 10.1016/j.eurpolymj.2024.112962
    [33]
    Zhong L, Du C, Liao G F, et al. Effects of backbone substituent and intra-ligand hydrogen bonding interaction on ethylene polymerizations with α-diimine nickel catalysts. Journal of Catalysis, 2019, 375: 113–123. doi: 10.1016/j.jcat.2019.05.026
    [34]
    Li A K, Ma H Y, Huang J L. Zirconium complexes bearing bis(phenoxy-imine) ligands with bulky o-bis(aryl)methyl-substituted aniline groups: synthesis, characterization and ethylene polymerization behavior. Applied Organometallic Chemistry, 2013, 27: 341–347. doi: 10.1002/aoc.2984
    [35]
    Li S K, Xu G Y, Dai S Y. A remote nonconjugated electron effect in insertion polymerization with α-diimine nickel and palladium species. Polymer Chemistry, 2020, 11: 2692–2699. doi: 10.1039/D0PY00218F
    [36]
    Liao Y D, Zhang Y X, Cui L, et al. Pentiptycenyl substituents in insertion polymerization with α-diimine nickel and palladium species. Organometallics, 2019, 38: 2075–2083. doi: 10.1021/acs.organomet.9b00106
    [37]
    Lu Z, Xu X W, Luo Y, et al. Unexpected effect of catalyst’s structural symmetry on the branching microstructure of polyethylene in late transition metal polymerization catalysis. ACS Catalysis, 2023, 13: 725–734. doi: 10.1021/acscatal.2c04525
    [38]
    Nie N, Wang Y Z, Tan C, et al. The synthesis of hyperbranched ethylene oligomers by nickel catalysts with oxazole structure. Journal of Catalysis, 2023, 428: 115164. doi: 10.1016/j.jcat.2023.115164
    [39]
    Zhong L, Zheng H D, Du C, et al. Thermally robust α-diimine nickel and palladium catalysts with constrained space for ethylene (co)polymerizations. Journal of Catalysis, 2020, 384: 208–217. doi: 10.1016/j.jcat.2020.02.022
    [40]
    Wang X L, Zhang Y P, Wang F, et al. Robust and reactive neutral nickel catalysts for ethylene polymerization and copolymerization with a challenging 1,1-disubstituted difunctional polar monomer. ACS Catalysis, 2021, 11: 2902–2911. doi: 10.1021/acscatal.0c04450
    [41]
    Gao J X, Yang B P, Chen C L. Sterics versus electronics: Imine/phosphine-oxide-based nickel catalysts for ethylene polymerization and copolymerization. Journal of Catalysis, 2019, 369: 233–238. doi: 10.1016/j.jcat.2018.11.007
    [42]
    Peng D, Pang W M, Xu G Y, et al. Facile synthesis of sterically demanding SHOP-type nickel catalysts for ethylene polymerization. Applied Organometallic Chemistry, 2019, 33: e5054. doi: 10.1002/aoc.5054
    [43]
    Peng D, He H L, Pang W M, et al. Synthesis of UHMWPE by neutral phosphine-phenolate based nickel catalysts. Polymer, 2023, 280: 126019. doi: 10.1016/j.polymer.2023.126019
    [44]
    Wang H, Lu W Q, Zou M M, et al. Direct synthesis of polyethylene thermoplastic elastomers using hybrid bulky acenaphthene-based α-diimine Ni(II) catalysts. Molecules, 2023, 28: 2266. doi: 10.3390/molecules28052266
    [45]
    Gong Y F, Li S K, Tan C, et al. π–π interaction effect in insertion polymerization with α-Diimine palladium systems. Journal of Catalysis, 2019, 378: 184–191. doi: 10.1016/j.jcat.2019.08.034
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